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[ CAS No. 306936-57-2 ] {[proInfo.proName]}

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Chemical Structure| 306936-57-2
Chemical Structure| 306936-57-2
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Product Details of [ 306936-57-2 ]

CAS No. :306936-57-2 MDL No. :MFCD01922131
Formula : C10H7FN2O Boiling Point : -
Linear Structure Formula :- InChI Key :CMXTUUXWJBLVEH-UHFFFAOYSA-N
M.W : 190.17 Pubchem ID :605439
Synonyms :

Calculated chemistry of [ 306936-57-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 49.37
TPSA : 45.75 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.44 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.14
Log Po/w (XLOGP3) : 1.44
Log Po/w (WLOGP) : 2.45
Log Po/w (MLOGP) : 1.22
Log Po/w (SILICOS-IT) : 3.1
Consensus Log Po/w : 1.87

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.38
Solubility : 0.801 mg/ml ; 0.00421 mol/l
Class : Soluble
Log S (Ali) : -2.01
Solubility : 1.87 mg/ml ; 0.00986 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.98
Solubility : 0.0198 mg/ml ; 0.000104 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.88

Safety of [ 306936-57-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 306936-57-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 306936-57-2 ]
  • Downstream synthetic route of [ 306936-57-2 ]

[ 306936-57-2 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 326-33-0 ]
  • [ 68-12-2 ]
  • [ 306936-57-2 ]
YieldReaction ConditionsOperation in experiment
79%
Stage #1: at 0 - 20℃; for 1 h;
Stage #2: at 80℃; for 2 h; Cooling with ice
Stage #3: Cooling with ice
Phosphoryl chloride (2.1 mL, 23mmol) was added dropwise to DMF (4.4mL, 57mmol) at 0°C. The resulting mixture was kept on stirring for 30 min at 0°C and then 30 min at room temperature. Reaction mixture was cooled in ice/water bath and 18 (1.96g, 10 mmol) was added slowly (not to exceed the temperature above 50°C) then heated to 80°C and stirred for 2h at this temperature. Reaction mixture was then poured into ice (15g), basified with 5N NaOH till pH 10 and stirred for 2h then acidified with concentrated HCl and continued to stir for additional 4h. Formed precipitates were filtered off, washed with small amount of water and dried under high vacuum to afford 1.5g (79percent) of aldehyde 19.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 18, p. 4932 - 4935
[2] Russian Journal of General Chemistry, 2005, vol. 75, # 5, p. 782 - 789
[3] Patent: WO2013/22766, 2013, A1, . Location in patent: Page/Page column 87
[4] European Journal of Medicinal Chemistry, 2017, vol. 133, p. 36 - 49
[5] Journal of Fluorine Chemistry, 2016, vol. 183, p. 59 - 68
  • 2
  • [ 326-33-0 ]
  • [ 306936-57-2 ]
YieldReaction ConditionsOperation in experiment
75%
Stage #1: at 0 - 70℃; for 4 h;
Stage #2: With sodium hydroxide In water at 60℃; for 0.0833333 h; Cooling
The ketone semicarbazone (14) (5 mmol) was added, portionwise with stirring, to a mixture of phosphorus oxychloride-dimethylformamide. The latter was prepared by the slow addition of POCl3 (1 1 mmol) to DMF (22mmol) at 0 ° C. The reaction mixture was heated at 60-70 C for about 4 hours and then poured onto cracked ice (10 g). The resulting mixture was neutralized with NaOH (2 g in 8 mL water), heated at 50-60 ° C for 5 minutes, and cooled. Impurities were then removed by filtration. The filtrate was acidified to pH - 5-6 using IO N HCl. The resulting precipitated solid was collected by filtration and washed with water. The product (2) was dried in the air (712 mg, 75percent). If needed, the solid was further purified by crystallization from ethanol/water. Melting point 163-165 c C; 1H NMR(CDCl3, 300MHz) 87.17-7.28(m, 3H, 0-ArH, -NH-), 7.69-7.74(m, 2H, m-ArH), 8.18(s, IH, Pyrazole), 9.97(s, IH, -CHO); EIMS 191(M++1)(12.62), 190(M+)(IOO, Base), 189(M+-H)(93.84); IR(Cm"1) 3165, 2897, 1646, 1517, 1481, 1250, 931; Anal. Calcd for C10H7FN2O : C, 63.16; H, 3.71 ; N, 14.73; Found : C, 63.16; H, 3.71; N, 15.06.
Reference: [1] Patent: WO2010/75290, 2010, A1, . Location in patent: Page/Page column 44-45
[2] Medicinal Chemistry, 2016, vol. 12, # 8, p. 751 - 759
  • 3
  • [ 120445-82-1 ]
  • [ 68-12-2 ]
  • [ 306936-57-2 ]
YieldReaction ConditionsOperation in experiment
600 mg
Stage #1: at 5 - 70℃; for 2 h;
Stage #2: at 0 - 70℃; for 1 h;
To a stirred solution of (E)-2-(1-(4-fluorophenyl)ethylidene)hydrazinecarboxamide (1 g, 5.12 mmol, 1.00 equiv) in N,N-dimethylformamide (5 mL) at 5° C. was added phosphorous oxychloride (5 mL) dropwise.
The resulting solution was stirred at 70° C. for 2 h.
The reaction mixture was cooled to 0° C. and quenched by the addition of 15 mL of ice/water mixture.
The pH value of the solution was adjusted to 7 with 4N sodium hydroxide solution.
The resulting mixture was stirred at 70° C. for an additional 1 h.
The reaction mixture was cooled back to room temperature.
The precipitate was collected by filtration and dried in a vacuum oven to give 600 mg (62percent) of 3-(4-fluorophenyl)-1H-pyrazole-4-carbaldehyde as a gray solid. LCMS (method A, ESI): RT=1.23 min, m/z=191.0 [M+H]+.
Reference: [1] Patent: US2014/323537, 2014, A1, . Location in patent: Paragraph 0214
  • 4
  • [ 403-42-9 ]
  • [ 306936-57-2 ]
Reference: [1] Russian Journal of General Chemistry, 2005, vol. 75, # 5, p. 782 - 789
[2] Patent: WO2013/22766, 2013, A1,
[3] Patent: US2014/323537, 2014, A1,
[4] European Journal of Medicinal Chemistry, 2017, vol. 133, p. 36 - 49
[5] Journal of Fluorine Chemistry, 2016, vol. 183, p. 59 - 68
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